Asymmetric solid-phase alkylation of ketones immobilized via SAMP hydrazone analogue linkers.
The preparation and application of new solid supports with chiral linkers, analogues of SAMP hydrazine on solid-phase, are described. The supports were used for immobilization of ketones (diethylketone, cyclohexanone, 4- tert-butylcyclohexanone), and diastereoselective alkylation of formed chiral ketone hydrazones. The enantiomeric purities of cleaved alpha-alkylated chiral ketones ranged from 10 to 73%. The use of chiral lithium amides for metalation of hydrazones of t-butylcyclohexanone increased the enantiomeric excess of the alkylated product by 25-47%.
Lazny
Ryszard
R
Institute of Chemistry, University of Bialystok, ul. Hurtowa 1, 15-399 Bialystok, Poland. lazny@uwb.edu.pl
Nodzewska
Aneta
A
Zabicka
Beata
B
D000478:Alkylation; D020650:Combinatorial Chemistry Techniques; D003432:Cross-Linking Reagents / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D010663:Phenylmercury Compounds / Q000737:chemistry
D003432:Cross-Linking Reagents; D006835:Hydrazones; D007659:Ketones; D010663:Phenylmercury Compounds; C036235:4-(4-sulfophenylazo)-2-mercuriphenol